About the job
WithCoverage delivers AI-driven risk management for companies facing complex insurance challenges. Clients include GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee, along with leaders in hospitality, construction, manufacturing, and defense contracting. The team replaces the traditional brokerage model by combining expert risk advisors with proprietary technology and an in-house Agency Management System. This platform gives both human and AI agents full access to policies, exposures, claims, billing, and commissions, supporting automation and informed decision-making.
Founded by JD Ross (Opendoor co-founder) and Max Brenner (Bain, Compound), WithCoverage has raised over $43M from investors such as Sequoia, 8VC, Khosla Ventures, and Crystal Venture Partners. The company’s mission is to fundamentally redefine risk management across the economy.
Role overview
This is the first dedicated Workplace and People Operations Associate at WithCoverage, based in New York City. The role focuses on building a strong workplace culture and ensuring smooth daily operations. More than just organizational tasks, this position aims to create an environment where employees can do their best work.
Why join
- Accelerated growth: WithCoverage is expanding quickly, creating opportunities to learn, lead, and influence both your career and the company’s direction.
- Impactful work: The company supports innovative brands in consumer goods, hospitality, and defense contracting.
- Industry innovation: Proprietary technology, automation, and AI are transforming a traditionally slow-moving field.
- Compensation and rewards: Competitive pay, meaningful equity, and strong benefits. The company values internal advancement and offers clear career growth paths.
What you will do
As the inaugural Workplace and People Operations Associate, this role has a direct impact on company culture and operational efficiency. The focus is on building a thriving environment for all employees and supporting the day-to-day needs of the team.

